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The Cleveland Browns have been one of the landmark professional football teams dating back to their establishment in 1946. They have had a long history of tradition and success in the National Football League. In recent times, though, the team has been extremely unsuccessful. After the franchise returned to Cleveland in 1999 as an expansion team, the team had a goal to become a Super Bowl caliber team within five years. However, they did not achieve this objective. The purpose of this study is to show why this did not happen. One of the major reasons for this was due to the choices that were made by the team’s front office. They made poor managerial decisions and player personnel selections through the NFL Draft and free agency. Through the use of newspaper articles, documentaries, books and interviews, this thesis explains what went wrong for the Browns and what the team’s front office should have done.